Ammonia → Sulfonium, triphenyl-, 7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-methanesulfonate (1:1)

Participants

Reaction Steps

Triphenylsulfonium iodide (390 mg; 1 mmol), ethyl orthoacetate (486 mg; 3 mmol), and camphorsulfonic acid (278 mg; 1.2 mmol) were dissolved in anhydrous methylene chloride (10 ml), and the resultant mixture was stirred for 12 hours at room temperature. The reaction mixture was alkalinized by adding 1% aqueous ammonia (10 ml), and subjected to extraction with methylene chloride three times, followed by drying. The solvent was removed through distillation, and the thus-obtained semi-solid matter was washed with ether, to thereby yield 410 mg of the target compound as white crystals (yield: 82%).

Provenance & Evidence